5 star rating: Highly Recommended 2 Reviews

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  • Location:Siena, Italy
  • Duration:8 hours (approx.)

Private Tour: Guided Hike in Tuscany with Transport from Siena

Explore Tuscany's picturesque rolling hills on a private, full-day hiking tour with transport from Siena. With your expert guide, enjoy a scenic, full-day adventurous hike through the beautiful Chianti region in Tuscany, full of lush vineyards and quaint villages, stopping halfway to relax over a picnic of classic Tuscan specialties. Continue in the afternoon by minivan to the medieval hill town of San Gimignano for a walk around its UNESCO World Heritage-listed city center. Spend time at your leisure in this gorgeous town before a relaxing drive back to Siena.


  • Private Tuscany hiking tour with transport from Siena
  • Hike through the vineyard-rich region of Chianti with your expert guide
  • Enjoy a picnic lunch in Chianti overlooking olive groves and vineyards
  • Explore the UNESCO World Heritage-listed town of San Gimignano at your leisure
  • Walk along the Via Francigena, an ancient pilgrimage road in San Gimignano
  • Private tour with an expert guide ensures a more personalized experience

What You Can Expect

Private Tour: Guided Hike in Tuscany with Transport from Siena

Private Tour: Guided Hike in Tuscany with Transport from Siena

Discover Tuscany’s famed natural beauty on this full-day tour from Siena! Your private hiking tour starts in the morning with a comfortable 40-minute drive by luxury minivan from Siena to the heart of Chianti. Chianti is a Tuscan region world-renowned for its picturesque vineyards and landscapes typified by lush green hills and olive groves.

Following your expert guide, unleash your inner adventurer on a scenic, leisurely-paced walk through the gorgeous Chianti countryside. Stop along the way to enjoy gelato or coffee (own expense) at a local café. At the end of the hike, your friendly guide will lead you to a spot where you can relax and enjoy a picnic of cured meats, locally grown vegetables, breads and cheeses, accompanied by a glass of wine.

After the picnic, you'll be picked up by air conditioned minivan and driven to San Gimignano, a colorful medieval hill town surrounded by vineyards that produce one of Tuscany’s most popular white wines, Vernaccia. Explore the town's breathtaking UNESCO World Heritage-listed city center, famous for its medieval architecture and panoramic views over Tuscany. Stroll down the Via Francigena path as your guide explains the history of this ancient pilgrimage road, said to link Rome to Canterbury in England.

After tracing the pilgrim's steps down Via Francigena, you'll have time for independent sightseeing in San Gimignano. See beautiful monuments in Piazza del Duomo and go inside the impressive cathedral (own expense), or browse the local shops for quality saffron spices that the town produces. In the late afternoon, meet your guide back at the minivan for the relaxing return journey to Siena.

Note: This hiking tour is suitable for those in good physical condition, and who have experience with long walks. Although the walking trails in Chianti are open to everyone, remember that the area is natural and unspoiled, so the ground can be uneven and, in some places, steep and narrow.

Customer Reviews

5 star rating: Highly Recommended June 2015

We had a great day with Jacopo. He tailored the hike to what we were interested in doing. Milo showed up with a great picnic lunch. Very enjoyable!

5 star rating: Highly Recommended July 2013

Milo picked us up at the arranged meeting place near the fortress in Sienna and drove us out to where we stared the beautiful walk through the vineyards. We chattered easily as we walked with Milo who enjoys good food and wine as much as we do. He was also able to give us an outline of the history of the Chainti area. Following our walk we drove to the scenic spot amongst the olive trees where Milo set up our picnic lunch. The afternoon visit to the two hilltop medieval villages gave us free time to explore and taste even more of " the worlds best gelati".

From USD $ 102.43

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Tour code: 5493TUSCANYTREK


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